2-Ethyl-2-oxazoline → N-[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl]propionamide

HRID 728808

Reaktionsgleichung

Reaktionsgleichung von HRID 728808
[CH2:1]([C:3]1[O:4][CH2:5][CH2:6][N:7]=1)[CH3:2].[N:8]1([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1>>[N:8]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:5][CH2:6][NH:7][C:3](=[O:4])[CH2:1][CH3:2])=[CH:15][CH:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Komponenten

3

Edukt 2

HCID 664122-Ethyl-2-oxazolineHCID 823151-(p-Hydroxyphenyl)imidazole

Produkt 1

HCID 14739903N-[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl]propionamide

Versuchsvorschrift

To 25 g (0.25 mol) of 2-ethyl-4,5-dihydrooxazole add 10.0 g (62 mmol) of 4-(1H-imidazol-1-yl)phenol. Reflux the reaction mixture. Monitor the progress of the reaction by thin-layer chromatography on silica gel (9:1, CH2Cl2 :MeOH). Upon completion of the reaction remove the excess starting material by distillation, add ethyl acetate, and wash the solution with 2 N NaOH. Dry the organic layer over anhydrous Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Recrystallization from ethyl acetate-hexane affords the title compound.

Aufarbeitung

  1. temperatureReflux the reaction mixture
  2. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (9:1, CH2Cl2 :MeOH)
  3. customUpon completion of the reaction remove the
  4. distillationby distillation
  5. additionadd ethyl acetate
  6. washwash the solution with 2 N NaOH
  7. dry with materialDry the organic layer over anhydrous Na2SO4
  8. customRemove the drying agent
  9. filtrationby filtration
  10. customremove the solvent in vacuo
  11. customRecrystallization from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-74fe83ecafe745bbb7106285e9382362
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051423

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